Nitrile hydratase enzymes in organic synthesis: Enantioselective synthesis of the lactone moiety of the mevinic acids

Room-temperature ionic liquids as replacements for organic solvents in multiphase bioprocess operations

“…The hydration of 1,3-DCB by the nitrile hydratase Rhodococcus 312 is a reaction of scientific and industrial interest-a number of illustrations already exist in the literature (e.g., Crosby et al, 1994;Maddrell et al, 1996;Martinkova et al, 1995). The substrate, however, is very poorly water soluble and the desired product 3-cyanobenzamide can be further hydrated by the second enzyme in the nitrile metabolism pathway, amidase, to yield the corresponding acid.…”

“…As an example of a two-phase biotransformation reaction, we will consider the Rhodococcus R312 catalyzed transformation of 1,3-dicyanobenzene (1,3-DCB) to 3-cyanobenzamide and 3-cyanobenzoic acid. The versatility of the Rhodococci for the biotransformation of nitriles (Bunch, 1998) and the synthetic applications of this enzyme system (Crosby et al, 1994;Maddrell et al, 1996) are well known. As an example of a liquid-liquid extraction process, we will consider the extraction of the polyketide antibiotic erythromycin-A.…”

Enantioselective Biotransformations of Nitriles in Organic Synthesis

“…The mechanism for region-and stereo-selective hydrolysis is far from clear. Nevertheless, the synthetic potential has been demonstrated in some biocatalytic desymmetrization reactions of prochiral dinitriles [46,[62][63][64][65][66].…”

Chemoenzymatic Approach to Enantiomerically Pure (R)‐3‐Hydroxy‐3‐methyl‐4‐pentenoic Acid Ester and Its Application to a Formal Total Synthesis of Taurospongin A

“…These results indicate that neither the nitrile hydratase nor the amidase in this microorganism worked in an enantioselective manner on the nitrile 5 or the intermediacy amide 7. While amidases had in many cases worked enantioselectively on b-alkoxy-and acyloxy-substituted nitriles, [16][17][18][19] the loss of stereoselection had also been observed when the substituent was altered from alkoxy and/or acyloxy to a hydroxy group. [16,[20][21] In this case, as the antipodal substrate, (S)-5 can be prepared from the enantiomerically pure form of (R)-epoxide 3, [3] this total procedure in Scheme 2 and Scheme 3 would also work well to provide (S)-1b.…”